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“Flipside,” an endearing, dizzying documentary about the crushing convergence between art and commerce, begins with a common cold open. What we presume to be our enigmatic subject, the late legendary jazz photographer Herman Leonard, offers us a few pearls of wisdom that have led to his success. An array of close-ups of the singular, black and white portraits he took of Duke Ellington, Frank Sinatra, and Nat King Cole, from a retrospective exhibition of his work, further instills his importance to an unknowing audience. These are also Leonard’s final days. He’s dying from cancer. From the opening, we think “Flipside” will be a “great man you must know more about” story.

But this documentary isn’t about the jazz photographer. At least, not directly. There are other stories: A woman writer battling writer’s block, “This American Life” creator Ira Glass’ musical, and the documentary’s primary inspiration,...